Chloroform → HCID 178518302, compound

HRID 2236835Notes

Reaction equation

HRID 2236835 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH:24]2[CH2:28][OH:29])=[CH:18][CH:17]=1.C(Cl)(Cl)Cl.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[Cl-].[S:48]1[CH:52]=[CH:51][CH:50]=[C:49]1[Zn+]>CN(C)C=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:29][CH2:28][CH:24]1[CH2:25][CH2:26][CH2:27][N:23]1[CH2:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][CH:14]=[C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:49]4[S:48][CH:52]=[CH:51][CH:50]=4)[CH:3]=3)[C:8](=[O:12])[NH:7][C:6]2=[O:13])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 178479833HCID 178479833, compoundHCID 178518260HCID 178518260, compound

Product 1

HCID 178518302HCID 178518302, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-Bromo-4-{[4-(2-hydroxymethyl-pyrrolidin-1-ylmethyl)-phenylamino]-methylene}-4H-isoquinoline-1,3-dione (100 mg, 0.2 mmol) in N,N-dimethylformamide (1 mL) is added Pd2(dba)3.CHCl3 (10 mg, 0.01 mmol) and P(tBu)3 (20 μL, 1 M solution in N,N-dimethylformamide, 0.02 mmol). After degassing the mixture, 2-thienyl zinc chloride (2.2 mL, 0.5 M solution in THF, 1.1 mmol) is then added and the resulting mixture is stirred for 2 h. N,N-dimethylformamide is then removed and the residue is purified through chromatography to provide the title compound (35 mg, 38%). MS (ESI): 460.1 (M+1)+1.

Workup

  1. additionis then added
  2. customN,N-dimethylformamide is then removed
  3. customthe residue is purified through chromatography

Sources & evidence

ORD record
ord-c099e470103441c9ba9663963eea2273
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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